In Chapter 16 of J.D. Salenger’s classic novel The Catcher in the Rye, Holden is visiting the city, New York, hoping to find a copy of a particular recording he believes his younger sister Phoebe will enjoy.  Holden, of course, is the quintessential alienated youth.  He is, in fact, the poster boy for social alienation.  His disdain for his contemporaries and for the average adult is offset by his love of children.  Children represent innocence and are untainted by the realities of life.  As he walks towards Broadway, site of his destination, a record story he hopes will have the record in question, he observes a family walking in front of him who Holden surmises probably just came from church.  It is Sunday, after all, and they simply gave that appearance.  What particularly captivates Holden, though, is the young boy, “a little kid about six years old” with a pretty voice who is singing a song the lyrics to which includes the refrain “if a body catch a body coming through the rye.”  As Holden describes his own reaction to this reaffirming episode, “[i]t made me feel better. It made me feel not so depressed any more.”

The lyrics Holden repeats are from a Robert Burns poem titled “Comin’ Thro’ the Rye.”  To Holden, the scene he observes depicts the innocence of youth.  Later, when he is home with his family, Holden is discussing the song with Phoebe, whose intelligence and common sense Holden values highly.  As he would expect, this ten-year-old girl is familiar with the Burns poem, informing Holden of its origins.  Holden then explains his feelings about the song the little boy had been singing and the effects the lyrics had on him:

“I keep picturing all these little kids playing some game in this big field of rye and all. Thousands of little kids, and nobody's around--nobody big, I mean--except me. And I'm standing on the edge of some crazy cliff. What I have to do, I have to catch everybody if they start to go over the cliff--I mean if they're running and they don't look where they're going I have to come out from somewhere and catch them. That's all I'd do all day. I'd just be the catcher in the rye and all. I know it's crazy, but that's the only thing I'd really like to be. I know it's crazy."

Holden’s love of children is taking the form of divine protector in his imagination, with the little boy’s song providing imagery consistent with his preconceived notions about life.  What he doesn’t realize, however, is that Burns’ poem and the song adapted from it carry less-than-innocent sexual connotations.  Holden’s misinterpretation of Burns’ poem lends this seminal character an element of innocence himself that his feelings of social alienation suggested might not otherwise exist.

Wow! Great question.  I would like to think that Holden would listen to music that is original in topic and genre.  He would not, as stated in #2, go for anything pop or overly played.  He would, most likely, stick to genres that were not rip-offs of other bands or artists.  Arguably, I could see him listening to something like The Eagles or The Hollies (On a Carousel), on his IPod, while watching Phoebe on the carousal.

On the other hand, I could see Holden listening to death metal (or other metal genres which speak to anger, hate, atheism).  I could see this based upon Holden's own internal conflicts so as to find an outlet.

I do find the post about bars relevant.  Holden does spend a lot of time in bars in the novel and, as out of character as it seems, likes to dance.  So, I guess I could see him in a bar grinding to Lady Gaga or Spears as well.

This is actually a pretty hard question! Way to go!

It might be easier to start with some songs Holden Caulfieldwouldn't like.  Holden Caulfield likely wouldn't like anything "phony" which would likely include most up and coming artists that got their start on American Idol, anything pop and/or popular among teenaged girls (Justin Beiber comes to mind), or anything overdone, like most of the new hip hop artists.

It is hard to imagine a present-day Holden Caulfield, but considering he spent a large part of the novel in bars, pretending to be older than he was, I imagine he'd be into obscure indy- bands and alternative music, as well as classic rock, anything influenced by blues and/or jazz and big band music.  Even now, I imagine he would be the type of kid to go through old LP's in his attic and get really interested in some of the good music of older generations.

I don't see him as "goth" or "emo" or any of the other current high school labels, as he desperately wanted to appear to be different (and above) everyone else.

Hmmm - a few come to mind. How about "Nowhere Man" by the Beatles? Or "American Idiot" by Greenday. Then there is "Faceless Man" by Creed. In the Country-Western vein, perhaps "Take this Job and Shove It." Also "Walking in My Shoes" by Depeche Mode and "Losing My Religion" by REM (these last ones are about alienation). "Forever Young" by Joan Baez - written by Bob Dylan (this song could relate to Holden's fear of growing up). Many songs by Bob Dylan would work - "Beyond Here Lies Nothing" or "Desloation Row" or "Life is Hard" or "Only a Pawn in their Game" or "Subterranean Homesick Blues" (you can tell what generation I am from!)

Good points, but the key is that he desperately wanted to appear different. So what kind of music would he listen to when no one was observing? I agree that he would not listen to the "contemporary pop" type of performers who seem to sound the same and sing the same. He would probably listen to bands that have a unique style or some unique message. With the suppressed anger and depression that Holden has rap and hard rock or heavy metal might appeal to his emotions.

The lyrics in the Green Day song, "Basket Case," can connect to Holden Caulfield in several ways.

Billie Jo Armstrong of Green Day said that he wrote the song because he believed that he was suffering from a mental illness: "The only way I could know what the hell was going on was to write a song about it."  This can be seen in the opening lyrics: "Do you have the time to listen to me whine / About nothing and everything all at once."  

Holden can be connected to this, as he often speaks about "nothing and everything," sometimes, "all at once." 

The song asks whether the listener has the time.  Holden presumes that the reader does.  In both settings, the narrator is going to lead the reader in a voyage through the mind, an exploration that is far from certain in terms of destination and end result.

The chorus of the song is another instance where there can be direct relation to Holden.  The chorus wonders about the condition of sanity:

Sometimes I give myself the creeps
Sometimes my mind plays tricks on me
It all keeps adding up
I think I'm cracking up
Am I just paranoid? 

Holden can be related to this chorus.  Holden's own unreliability, his questioning about his identity and about whether or not he is insane are all instances where he can be related to the lyrics.  

There is a self-questioning about his place in the world, one filled, in his view, with "phonies."  Consequently, as expressed in the song, Holden is uncertain about his own condition and place in the world, like the words of the chorus of "Basket Case" suggest.

Invariably, your song list would encompass songs that address both Holden's temperament as well as the themes.  For example, one theme that would represent Holden's love of innocence as well as the sad lament he feels for the love and eventual separation for his sister would be Judy Collins' "Both Sides, Now."  There is an innocence borne out of experience in the song that would forge some strong connection to Holden and his predicament in the narrative.  I think that another song that would connect to the theme of Holden's disdain for phonies would be Pink Floyd's "Comfortably Numb."  There is an alienation featured in the song that would relate to the dislodging that Holden feels in a society that places such a primacy on phonies and being conformist at the cost of individual voice.  I think that Holden would use the Trent Reznor's song, "Hurt," to also bring out this particular disdain for the phoniness and conformity that he can only rage against, with little consequence regarding changing it.  The theme of the hatred towards authority figures would be seen in a song like R.E.M.'s "It's the End of the World."  There is a frenetic pace to the song that represents how Holden would feel that individuals in the position of power have done a fairly good job of ruining the world and any hope of redemption within it.  Holden could identify with the idea of "I feel fine," in a setting through which conformity has resulted in a apocalyptic reality.  I think that the song that yearns for innocence and reflects the hurt, anger, and melancholy that is such a part of Holden's narrative would the The Turtles' "Happy Together."  There is the haunting and reverberating echo of "Happy Together" that comes through the song when Holden's world is one in which he really is not together with anyone.  In this song, there is a sad and ironic disconnect between the lyrics of the song, Holden's experienced, and his potential for hope and dreams.  In this, I think that an added dimension becomes present in both the songs and Holden's reaction to them.

I would use 'Smells Like Teen Spirit' by Nirvana to express Holden's sense of alienation and boredom. Similarly I would add 'Loser' by Beck, illustrating his sense of hopelessness.

I love the Green Day choice as highlighted above, but I would add 'Basketcase' as well. The opening lines of the song are very reflective of the opening of the novel -

Do you have the time
To listen to me whine
About nothing and everything
All at once

I've got two ideas for songs.

First, what about "American Idiot" by Green Day.  That song, to me, is basically saying that everyone in America who is relatively "normal" -- everyone who is like everyone else -- is an idiot.  That's Holden's attitude in my mind.

Second, how about "Welcome to My Life" by Simple Plan.  That seems like a great song for Holden because it's all about how much the person's life sucks and how they feel like everyone hates them.

So I think those two songs would appeal to Holden because he feels like the world is oppressing him and that everyone else is shallow and stupid.

There are so many songs about feeling alienated, but the song that first came to my mind was “Watching the Wheels “ by John Lennon.  I guess that is a bit of a morbid suggestion!  However, the song does have a kind of melancholy reflectiveness to it.  You can read the lyrics here:

http://www.oldielyrics.com/lyrics/john_lennon/watching_the_wheels.html

InThe Catcher in the Rye, Holden's loneliness remains a major theme throughout the novel.  He attempts to solve his feelings of alienation through companionship, but ultimately his lack of people skills and genuine insecurity undermine his ability to develop relationships on a deeper level. 

A rap or hip-hop song that relates to the theme of loneliness in The Catcher in the Rye, and especially Holden's feelings of isolation is Drake's "I Get Lonely Too."  The lyrics definitely reflect Holden Caulfield's wishful attempts at finding someone to connect with:

Take Me,to another place where I’ll beface to face, just you and mewith no rules, just like youI get lonely too ("I Get Lonely Too")

Holden would rather be in "another place" as Drake's song suggests, a place free of the difficulties and confusing "rules" of adulthood.  In the lyrics from Drake's song, Holden could envision himself in the pastoral scene from "The Catcher in the Rye" song, safe in his childish dreams and not wanting for companionship.

Songs that speak to a desire to escape one's current situation would be appropriate for the early chapters of the novel. One such is "We Gotta Get Outta this Place," a 1965 hit for a band named The Animals. Because Holden is eager to leave the phonies at Pencey Prep, the lyrics

We gotta get out of this place
If it's the last thing we ever do
We gotta get out of this place
'cause girl, there's a better life for me and you

are resonant, and could be revisited during his date with Sally Hayes when he asks her to marry him and escape to New England.

The 1982 Whitesnake hit "Here I Go Again" is also fitting in that it describes Holden's feelings of loneliness, alienation, and uncertainty:

No, I don't know where I'm goin'
But I sure know where I've been
Hanging on the promises in songs of yesterday
And I've made up my mind
I ain't wasting no more time

The song "Sugar Mountain," written by Neil Young in 1964 on his nineteenth birthday, relates poignantly not only to Holden's desire to remain young, but also to his growing realization that childhood must end for everyone.

Oh, to live on Sugar Mountain
With the barkers and the colored balloons,
You can't be twenty on Sugar Mountain
Though you're thinking that
you're leaving there too soon,
You're leaving there too soon.

Another verse of "Sugar Mountain" speaks to Holden's attempts to enter the adult world by smoking cigarettes and imagining himself as a tough guy. He tries on some adult behaviors much like these:

Now you're underneath the stairs
And you're givin' back some glares
To the people who you met
And it's your first cigarette

and

Now you say you're leavin' home
'Cause you want to be alone.
Ain't it funny how you feel
When you're findin' out it's real?

And finally, "The Circle Game," written and recorded by Joni Mitchell for her 1970 album Ladies of the Canyon, offers a fitting end to the novel. Because of the motif of the carousel, it seems the perfect expression of Holden's feelings as he watches Phoebe on the carousel but does not join her. The Central Park carousel has been a place of joy for him, but he has outgrown it. It is a beautifully bittersweet moment when he is content to watch his young sister enjoying herself.

Yesterday a child came out to wonder
Caught a dragonfly inside a jar
Fearful when the sky was full of thunder
And tearful at the falling of a star
And the seasons they go round and round
And the painted ponies go up and down
We're captive on the carousel of time
We can't return we can only look behind
From where we came
And go round and round and round
In the circle game

Then the child moved ten times round the seasons
Skated over ten clear frozen streams
Words like, when you're older, must appease him
And promises of someday make his dreams
And the seasons they go round and round
And the painted ponies go up and down
We're captive on the carousel of time
We can't return we can only look behind
From where we came
And go round and round and round
In the circle game

Sixteen springs and sixteen summers gone now
Cartwheels turn to car wheels through the town
And they tell him,
Take your time, it won't be long now
Till you drag your feet to slow the circles down
And the seasons they go round and round
And the painted ponies go up and down
We're captive on the carousel of time
We can't return we can only look behind
From where we came
And go round and round and round
In the circle game

So the years spin by and now the boy is twenty
Though his dreams have lost some grandeur coming true
There'll be new dreams, maybe better dreams and plenty
Before the last revolving year is through
And the seasons they go round and round
And the painted ponies go up and down
We're captive on the carousel of time
We can't return, we can only look behind
From where we came
And go round and round and round
In the circle game

And go round and round and round
In the circle game

The song that you are referring to is "Little Shirley Beans," the record that Holden bought for his sister and subsequently broke before he was able to give it to her. 

Another song that is relevant to Phoebe and all children is the song that Holden hears a little boy singing when he is in NYC, and that he believes captures the essence of what he would like to be as a grown-up has to do with being a catcher in the rye.

"Instead, he can only imagine being a catcher in the rye who stands at the edge of a large rye field watching over and protecting little kids from danger."

"You know that song, 'If a body catch a body comin' through the rye'? I'd like—"

"It's 'If a body meet a body coming through the rye!'" old Phoebe said. "It's a poem. By Robert Burns."

Phoebe's primary traits are loyalty and innocence, as seen in her dealings with Holden. She is also organized and has a sense of romance or poetry, as seen in the way she keeps her room at home, in her writing, and in her act of packing a bag to go with Holden wherever he is going. 

"Going to California" might be a good song for Phoebe. She is ready to leave to follow a dream...

I would pick different songs from different periods in music to capture much of Phoebe's eclectic and engaging temperament.  The first song I would pick would be from The Beatles' last album, "Abbey Road."  Harrison's "Here Comes the Song" is probably one of the most intensely poetic and tender songs from the group.  Listened in context, it appears right after the song, "I Want You (She's So Heavy)" which is a long and intense ranting type of song, heavy with the group's dabbling in a type of metal.  The song is so dreary and intent on moving the listener into a type of other world with its repetition and almost "angry" tone.  This is juxtaposed nicely with "Here Comes the Song," a song that emphasizes that after the rain, the sun will emerge.  In my mind, this is a great contraposition between Holden and Phoebe, who represents much of the spirit of positive energy and vibrance that Holden is not.  This is similar to "Here Comes the Sun" which represents much of "I Want You (She's So Heavy)" could only hope to embody:  "Little darling, I feel that ice is slowly melting."

Another song that I would use to represent Phoebe's sense of authenticity and purity would be another Beatles' song, "In My Life."  The song is a reverie about the "places and things" that one remembers in one's life.  Phoebe's impact on Holden, and how he envisions himself as a "catcher in the rye" and watching over Phoebe while on the merry- go- round would represent the same level of tender reflection that is captured in the song:  "In my life, I've loved you more."

In terms of articulating the pain of leaving and the oddly simultaneous feeling of wanting to stay with someone while wanting to leave, The Rolling Stones' song, "Angie," would be a great song that captures both Holden's feeling of wanting to leave, but being doggedly pursued by the feeling of not being able to go.  I can imagine this song playing when Phoebe has her suitcase, intending to go along with him: "Ain't it time to say goodbye?"

I have always felt that the relationship between Holden and Phoebe is where the former is troubled water and the latter is willing to be a bridge to happier sentiments and stronger emotional connection.  In this light, I sense that Simon and Garfunkel's "Bridge over Troubled Water" speaks quite powerfully to this sentiment.  The opening lines could be spoken by Phoebe to Holden:  "When you're weary/ feeling small/ when tears are in your eyes/ I'll dry them off."  I think Phoebe demonstrates the emotional sensitivity to be that sentimental "bridge" over Holden's troubled waters.

In J. D. Salinger's Catcher in the Rye, Holden has two dorm mates who are foils of each other and Holden: Robert Ackley and Ward Stradlater.  The former is a "pigpen"; the latter a "playboy."

Ackley's unhygienic personal habits annoy Holden to no end: he cuts his toenails and leaves the clippings on Holden's floor; he sifts through Holden's personal belongings.  He's an invasion of Holden's personal privacy and intimate space.  As a pejorative, Holden calls him "Ackley Kid."  He may be a bigger "nerd" than Holden.  He reminds me of "Shy Ronnie" by Andy Samberg from the Saturday Night Live Digital Short with Rihanna.

Some other good songs that relate to Ackley or that Holden would like to play for Ackley when he invades are:

• "Rude Boy" - Rihanna
• "Space Invader" - The Pretenders
• "Everything In Its Right Place" - Radiohead
• "Dirty Deeds Done Dirt Cheap" - AC/DC
• anything by Nine Inch Nails ("March of the Pigs" or "Piggy" perhaps?)

My answer is a little tangential, but the question reminded me of a story by James Thurber titled "One is a Wanderer." It was reprinted in the collection titled The Middle-Aged Man on the Flying Trapeze and again in The Thurber Carnival. The mood of Thurber''s story is very similar to that of The Catcher in the Rye although there are many differences. Salinger's novel is about a teenager, while Thurber's story is about a middle-aged man. But both are lonely wanderers looking for something in New York, a city where that "something" is notoriously in short supply. They are looking for human contact, sincerity, friendship, even love that doesn't have to be bought and paid for. The protagonist of "One is a Wanderer" is not given a name. It seems fair to assume that Thurber is writing about his own personal experience. Like Holden Caulfield, he knows his way around Manhattan. And like Holden Caulfield, he is constantly on the move, thinking he might go here or he might go there. For example:

I think maybe I'll call the Bradleys, he thought, getting up out of his chair. And don't, he said to himself, standing still a moment, don't tell me you're not cockeyed now, because you are cockeyed now, just as you said you wouldn't be when you got up this morning and had orange juice and coffee and determined to get some work done, a whole lot of work done; just as you said you wouldn't be but you knew you would be, all right. You knew you would be, all right.

Like Holden who keeps thinking about Jane Gallagher, Thurber's protagonist has a woman in his life who never appears in the story. Her name is Marianne. He thinks about her but is reluctant to go to see her--perhaps because he is a little afraid she might not want to see him. Instead he considers seeing everybody else who might be available.

There were several people in Dick and Joe's that he knew. There were Dick and Joe, for two--or, rather, for one, because he always thought of them as one; he could never tell them apart. There were Bill Vardon and Mary Wells. Bill Vardon and Mary Wells were a little drunk, and gay. He didn't know them very well, but he could sit down with them. . . .

There is such an impressive similarity between James Thurber's "One is a Wanderer" and J. D. Salinger's The Catcher in the Rye that it seems likely Salinger was inspired, consciously or unconsciously, by reading the older author's melancholy, introspective tale. --But what about the original question, "What is a good choice of a song that would describe The Catcher in the Rye?" In "One is a Wanderer" the protagonist keeps remembering a jazz song that was very popular in his day.

He became conscious of the song he was whistling . . . and walked out of the room to the elevator, and there he began to sing the last part of the song. "Make my bed and light the light, for I'll be home late tonight, blackbird, bye bye."

So this song titled "Bye Bye, Blackbird," though it dates back to the era chronicled in F. Scott Fitzgerald's novel The Great Gatsby, might be appropriate as a choice for a song that would describe The Catcher in the Rye. The song, for those who remember the sad and sprightly tune, haunts Thurber's story, even when the lyrics are not being quoted. He repeats some of the refrain at the very end of "One is a Wanderer."

When he got to his room, he lay down on the bed a while and smoked a cigarette. He found himself feeling drowsy and he got up. He began to take his clothes off, feeling drowsily contentented, mistily contented. He began to sing, not loudly, because the man in 711 would complain. The man in 711 was a gray-haired man, living alone . . . and analyzer . . . a rememberer . . .

"Make my bed and light the light, for I'll be home late tonight . . . "

This is obviously a great question that could be answered in a number of different ways, depending on the kind of themes that are apparent in your own reading of this text. For me, one of the key and tragic themes is that of loneliness. The way in which Holden chooses to isolate himself from everybody else around him is very moving and sad. Note, for example, how even in the first chapter, he has clearly chosen to keep himself away from everybody else:

Anyway, it was the Saturday of the football game... I remember around three o'clock that afternoon I was standing way the hell up on top of Thomsen Hill... You could see the whole field from there, and you could see the two teams bashing each other all over the place... You could hear them all yelling.

This is our first indication in the novel that Holden is a character who deliberately seeks to keep himself away from everybody else, even though ironically he actually desires human company. Think of when he goes into a phonebox and stays there for twenty minutes, wanting to ring somebody but not being able to select anybody. An excellent song that deals with the theme of loneliness is "Eleanor Rigby" by the Beatles. This would be a good song to select in order to highlight this particular element of the text, as just like Eleanor Rigby and Father Mackenzie in the song, Holden is a character who is desperately lonely and craving relationship with humans.

Both your question, and the anti-school atmosphere in the novel Catcher in the Rye by the recently deceased J.D. Salinger remind me of the depressing lyrics of a song by Bob Geldof's original Irish band "The Boomtown Rats" The song is called, (appropriately!) "I Don't Like Mondays" and opens with a vision of a mom/teenage girl on a typically dreary Monday morning on a schoolday. The melody is very atmospheric/minor key and the words suggest a hard-knock life in a grey impoverished estate. "Nobody's gonna go to school today" and "her momma can't stand it, and her poppa can't stand it" In the end I think she mitches off school and runs away. Sadly it was based on a girl who shot people and was banned in the U.S. Also, Pink Floyd "Leave them kids alone" from "Brick in the Wall."

Ha ha! What a funny question. There is a song from the 60's rock band, The Kinks, that reminds me of Ackley. It is called Well Respected Man. It is a British rock group, so you will have to "translate" some of the words, but it is about an annoying hypocrite that is "well respected" about town, but really a jerk. See the link below for the words.

Also, another song that comes to mind is You're So Vain by Carly Simon. It is also about a person that is pretty impressed with himself/herself - "You're so vain, you probably think this song is about you......" etc.

Simon supposedly wrote this song with a specific person in mind, but over the years, many have tried to speculate as to the identify of the song's subject. Some have guessed Warren Beatty, the actor. Others have guessed Mick Jagger, David Geffin and a host of other celebrities.

The reason that these two songs could be good with reference to Ackley is because they both are about rich people. Since Cather in the Rye is not about poor people but rather young men whose families can afford to send them to expensive prep schools like Pencey Prep, these would be good songs to use.

Perhaps some younger person would have better examples from more modern times, but I'm a child of the 60's so these two songs come to my mind.